Palifosfamide | ZIO-201 | CAS#31645-39-3 | 1070409-31-2 | DNA cross-linker

Palifosfamide-Tris
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202130

CAS#: 1070409-31-2 (tris salt)

Description: Palifosfamide, also known as ZIO201, is a synthetic mustard compound with potential antineoplastic activity. An active metabolite of ifosfamide covalently linked to the amino acid lysine for stability, palifosfamide irreversibly alkylates and cross-links DNA through GC base pairs, resulting in irreparable 7-atom inter-strand cross-links; inhibition of DNA replication and cell death follow. Unlike ifosfamide, this agent is not metabolized to acrolein or chloroacetaldehyde, metabolites associated with bladder and CNS toxicities. In addition, because palifosfamide does not require activation by aldehyde dehydrogenase, it may overcome the tumor resistance seen with ifosfamide.

Chemical Structure

Palifosfamide-Tris

CAS# 1070409-31-2 (tris salt)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 202130
Name: Palifosfamide-Tris
CAS#: 1070409-31-2 (tris salt)
Chemical Formula: C8H22Cl2N3O5P
Exact Mass: 0.00
Molecular Weight: 342.154
Elemental Analysis: C, 28.08; H, 6.48; Cl, 20.72; N, 12.28; O, 23.38; P, 9.05

Price and Availability

Size	Price	Availability	Quantity
10mg	USD -2
25mg	USD -2
50mg	USD -2
100mg	USD -2
200mg	USD -2
500mg	USD -2
1g	USD -1
2g	USD -1
5g	USD -1
10g	USD -1
20g	USD -1
50g	USD -1
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 1070409-31-2 (tris salt); 31645-39-3 (free acid)

Synonym: ZIO201; ZIO-201; ZIO 201; IPAM; NSC 297900; NSC-297900; NSC297900; isophosphoramide mustard; Palifosfamide. Palifosfamide tris salt; Trade name: Zymafos.

IUPAC/Chemical Name: 2-amino-2-(hydroxymethyl)propane-1,3-diol;bis(2-chloroethylamino)phosphinic acid

InChi Key: PGLRCMRTUIMSFQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H11Cl2N2O2P.C4H11NO3/c5-1-3-7-11(9,10)8-4-2-6;5-4(1-6,2-7)3-8/h1-4H2,(H3,7,8,9,10);6-8H,1-3,5H2

SMILES Code: ClCCNP(NCCCl)(O)=O.OCC(CO)(N)CO

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not soluble in water.

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Palifosfamide (ZIO-201) is currently developed by ZIOPHARM Oncology, Inc. It is a proprietary stabilized metabolite of ifosfamide. Ifosfamide has been shown to be effective in high doses in treating testicular cancer, sarcoma and lymphoma. Ifosfamide-based treatment generally represents the standard of care for sarcoma; however, it is not approved by the FDA in this indication. Ifosfamide metabolites include acrolein and chloroacetaldehyde, both highly toxic. Preclinical studies have shown that palifosfamide has activity in leukemia and solid tumor cancers. These studies also indicate that palifosfamide has a better safety profile than ifosfamide, likely because the toxic metabolites of ifosfamide, acrolein and chloroacetaldehyde are not present in palifosfamide. We believe the administration of palifosfamide may avoid many of the toxicities of ifosfamide without compromising the activity of the drug. see ZIOPHARM's website: http://www.ziopharm.com/clinical_zio201.php.

Product Data:

Product Data

Instruction:

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Biological target:	Palifosfamide, also known as ZIO201, is a synthetic mustard compound with potential antineoplastic activity.
In vitro activity:	The cytotoxic effect of palifosfamide lysine was studied in osteosarcoma (OS), Ewing's sarcoma (ES) and rhabdomyosarcoma (RMS) cell lines using the MTT assay. Palifosfamide lysine was cytotoxic against all the cell lines tested with the IC(50) ranging from 0.5 to 1.5 microg/ml except for OS222, which had an IC(50) of 7 microg/ml. Reference: Cancer Chemother Pharmacol. 2009 Sep;64(4):733-40. https://pubmed.ncbi.nlm.nih.gov/19224214/
In vivo activity:	The antitumor activities of stabilized palifosfamide were investigated in vivo. Dose response, route and schedule of administration, and interaction with docetaxel or doxorubicin were investigated in NCr-nu/nu mice bearing established orthotopic mammary MX-1 tumor xenografts. Oral activity was investigated in P388-1 leukemia in CD2F1 mice. Oral and intraperitoneal bioavailabilities were compared in Sprague-Dawley rats. Stabilized palifosfamide administered by optimized regimens suppressed MX-1 tumor growth (P<0.05) by greater than 80% with 17% complete antitumor responses and up to three-fold increase in time to three tumor doublings over control. Reference: Anticancer Drugs. 2012 Feb;23(2):173-84. https://pubmed.ncbi.nlm.nih.gov/22027537/

Preparing Stock Solutions

The following data is based on the product molecular weight 342.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Hingorani P, Zhang W, Piperdi S, Pressman L, Lin J, Gorlick R, Kolb EA. Preclinical activity of palifosfamide lysine (ZIO-201) in pediatric sarcomas including oxazaphosphorine-resistant osteosarcoma. Cancer Chemother Pharmacol. 2009 Sep;64(4):733-40. doi: 10.1007/s00280-008-0922-4. Epub 2009 Feb 18. PMID: 19224214. 2. Jones B, Komarnitsky P, Miller GT, Amedio J, Wallner BP. Anticancer activity of stabilized palifosfamide in vivo: schedule effects, oral bioavailability, and enhanced activity with docetaxel and doxorubicin. Anticancer Drugs. 2012 Feb;23(2):173-84. doi: 10.1097/CAD.0b013e32834d73a6. PMID: 22027537.
In vitro protocol:	1. Hingorani P, Zhang W, Piperdi S, Pressman L, Lin J, Gorlick R, Kolb EA. Preclinical activity of palifosfamide lysine (ZIO-201) in pediatric sarcomas including oxazaphosphorine-resistant osteosarcoma. Cancer Chemother Pharmacol. 2009 Sep;64(4):733-40. doi: 10.1007/s00280-008-0922-4. Epub 2009 Feb 18. PMID: 19224214.
In vivo protocol:	1. Jones B, Komarnitsky P, Miller GT, Amedio J, Wallner BP. Anticancer activity of stabilized palifosfamide in vivo: schedule effects, oral bioavailability, and enhanced activity with docetaxel and doxorubicin. Anticancer Drugs. 2012 Feb;23(2):173-84. doi: 10.1097/CAD.0b013e32834d73a6. PMID: 22027537.

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1: Williams R. Discontinued in 2013: oncology drugs. Expert Opin Investig Drugs. 2015 Jan;24(1):95-110. Epub 2014 Oct 14. PubMed PMID: 25315907.

2: Movva S, Verschraegen C. Systemic management strategies for metastatic soft tissue sarcoma. Drugs. 2011 Nov 12;71(16):2115-29. doi: 10.2165/11594500-000000000-00000. Review. PubMed PMID: 22035513.

3: Jones B, Komarnitsky P, Miller GT, Amedio J, Wallner BP. Anticancer activity of stabilized palifosfamide in vivo: schedule effects, oral bioavailability, and enhanced activity with docetaxel and doxorubicin. Anticancer Drugs. 2012 Feb;23(2):173-84. doi: 10.1097/CAD.0b013e32834d73a6. PubMed PMID: 22027537.

4: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Dec;31(10):661-700. PubMed PMID: 20140276.

5: Jung S, Kasper B. Palifosfamide, a bifunctional alkylator for the treatment of sarcomas. IDrugs. 2010 Jan;13(1):38-48. Review. PubMed PMID: 20024846.

6: Hingorani P, Zhang W, Piperdi S, Pressman L, Lin J, Gorlick R, Kolb EA. Preclinical activity of palifosfamide lysine (ZIO-201) in pediatric sarcomas including oxazaphosphorine-resistant osteosarcoma. Cancer Chemother Pharmacol. 2009 Sep;64(4):733-40. doi: 10.1007/s00280-008-0922-4. Epub 2009 Feb 18. PubMed PMID: 19224214.

7: Anderson P, Aguilera D, Pearson M, Woo S. Outpatient chemotherapy plus radiotherapy in sarcomas: improving cancer control with radiosensitizing agents. Cancer Control. 2008 Jan;15(1):38-46. Review. PubMed PMID: 18094659.

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Palifosfamide-Tris featured